Modern Aspects of the Smiles RearrangementCitation formats

Standard

Modern Aspects of the Smiles Rearrangement. / Holden, Catherine; Greaney, Michael.

In: Chemistry: A European Journal, Vol. 23, 2017, p. 8992–9008.

Research output: Contribution to journalArticle

Harvard

Holden, C & Greaney, M 2017, 'Modern Aspects of the Smiles Rearrangement', Chemistry: A European Journal, vol. 23, pp. 8992–9008. https://doi.org/10.1002/chem.201700353

APA

Holden, C., & Greaney, M. (2017). Modern Aspects of the Smiles Rearrangement. Chemistry: A European Journal, 23, 8992–9008. https://doi.org/10.1002/chem.201700353

Vancouver

Holden C, Greaney M. Modern Aspects of the Smiles Rearrangement. Chemistry: A European Journal. 2017;23:8992–9008. https://doi.org/10.1002/chem.201700353

Author

Holden, Catherine ; Greaney, Michael. / Modern Aspects of the Smiles Rearrangement. In: Chemistry: A European Journal. 2017 ; Vol. 23. pp. 8992–9008.

Bibtex

@article{8305925c05c94f53aaf206cef356b46f,
title = "Modern Aspects of the Smiles Rearrangement",
abstract = "The Smiles rearrangement is an intramolecular SNAr reaction, breaking a C−X single bond and forming a new C−X or C−C bond though ipso substitution. Its vast scope, in terms of nucleophile, leaving group, and ring-size of the transition state, make it a powerful tool for arene functionalization, as it can be employed strategically to switch easily-forged bonds with more difficult connections that would be challenging to realize in the intermolecular mode. The reaction has received significantly renewed attention in recent years, as advances in areas such as arene C−X bond formation and radical generation have been harnessed for new arene syntheses through Smiles chemistry. In addition, new reaction modes have been discovered, such as the Clayden rearrangement of lithiated ureas, creating innovative applications for Smiles rearrangements in asymmetric arylation. This Minireview will discuss advances in these areas in the recent literature, covering both two-electron, polar Smiles rearrangements along with single-electron radical transformations.",
author = "Catherine Holden and Michael Greaney",
year = "2017",
doi = "10.1002/chem.201700353",
language = "English",
volume = "23",
pages = "8992–9008",
journal = "Chemistry: A European Journal",
issn = "0947-6539",
publisher = "John Wiley & Sons Ltd",

}

RIS

TY - JOUR

T1 - Modern Aspects of the Smiles Rearrangement

AU - Holden, Catherine

AU - Greaney, Michael

PY - 2017

Y1 - 2017

N2 - The Smiles rearrangement is an intramolecular SNAr reaction, breaking a C−X single bond and forming a new C−X or C−C bond though ipso substitution. Its vast scope, in terms of nucleophile, leaving group, and ring-size of the transition state, make it a powerful tool for arene functionalization, as it can be employed strategically to switch easily-forged bonds with more difficult connections that would be challenging to realize in the intermolecular mode. The reaction has received significantly renewed attention in recent years, as advances in areas such as arene C−X bond formation and radical generation have been harnessed for new arene syntheses through Smiles chemistry. In addition, new reaction modes have been discovered, such as the Clayden rearrangement of lithiated ureas, creating innovative applications for Smiles rearrangements in asymmetric arylation. This Minireview will discuss advances in these areas in the recent literature, covering both two-electron, polar Smiles rearrangements along with single-electron radical transformations.

AB - The Smiles rearrangement is an intramolecular SNAr reaction, breaking a C−X single bond and forming a new C−X or C−C bond though ipso substitution. Its vast scope, in terms of nucleophile, leaving group, and ring-size of the transition state, make it a powerful tool for arene functionalization, as it can be employed strategically to switch easily-forged bonds with more difficult connections that would be challenging to realize in the intermolecular mode. The reaction has received significantly renewed attention in recent years, as advances in areas such as arene C−X bond formation and radical generation have been harnessed for new arene syntheses through Smiles chemistry. In addition, new reaction modes have been discovered, such as the Clayden rearrangement of lithiated ureas, creating innovative applications for Smiles rearrangements in asymmetric arylation. This Minireview will discuss advances in these areas in the recent literature, covering both two-electron, polar Smiles rearrangements along with single-electron radical transformations.

U2 - 10.1002/chem.201700353

DO - 10.1002/chem.201700353

M3 - Article

VL - 23

SP - 8992

EP - 9008

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

ER -